Reaktionsgleichung
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([N:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]2)[CH:11]=[CH:10][CH:9]=1.[I:28]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[OH:1][C:2]1[C:7]([I:28])=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([N:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:16]=[N:15]2)[CH:11]=[CH:10][CH:9]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a suspension of the title compound from Example 5 Step B (4.0 g, 10.6 mmol) and silver sulfate (3.31 g, 10.6 mmol) in ethanol (20 mL) was added iodine (2.69 g, 10.6 mmol), and the resulting mixture was vigorously stirred at room temperature. After 2 h, the reaction mixture was quenched with water and sodium bisulfite solution, extracted with ethyl acetate and concentrated in vacuo. Purification by chromatography on silica gel (0 to 15% EtOAc in hexanes, then 15 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 503.7 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 13.08 (s, 1 H),8.17 (s, 1 H),8.10 (t, J=8.0 Hz, 1 H),8.06 (d, J=8.0 Hz, 1 H),7.86 (dd, J=7.5, 1.5 Hz, 1 H),7.82 (dd, J=8.0, 1.5 Hz, 1 H),7.52 (d, J=7.5 Hz, 1 H),6.75 (t, J=8.0 Hz, 1 H),4.33 (q, J=7.0 Hz, 2 H),1.43 (t, J=7.0 Hz, 3 H).
Aufarbeitung
- customthe reaction mixture was quenched with water and sodium bisulfite solution
- extractionextracted with ethyl acetate
- concentrationconcentrated in vacuo
- customPurification by chromatography on silica gel (0 to 15% EtOAc in hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-7b61031f9a654ce497ca5abba1cdc449
- Quelldatensatz
- uspto-grants-2014_11
- Patentnummer
- US08895583B2
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